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CHEBI:194134 - hemiustilaginoidin D

ChEBI IDCHEBI:194134
ChEBI Namehemiustilaginoidin D
Stars
DefinitionA naphtho-γ-pyrone which carries hydroxy substituents at positions C-5, C-6 and C-8 and methyl groups at C-2 and C-3. Obtained from the laccase gene deletion mutant of Villosiclava virens (anamorph: Ustilaginoidea Virens), it is a precursor of ustilaginoidins used as the raw material for hapten synthesis through diazotization and Mannich reactions followed by bioconjugation with carrier proteins for complete antigen synthesis.
Last Modified22 November 2022
SubmitterMarcus Ennis
DownloadsMolfile
FormulaC15H14O5
Net Charge0
Average Mass274.272
Monoisotopic Mass274.08412
SMILESC[C@H]1Oc2cc3cc(O)cc(O)c3c(O)c2C(=O)[C@@H]1C
InChIInChI=1S/C15H14O5/c1-6-7(2)20-11-4-8-3-9(16)5-10(17)12(8)15(19)13(11)14(6)18/h3-7,16-17,19H,1-2H3/t6-,7-/m1/s1
InChIKeyHYXVOKDJTASVDZ-RNFRBKRXSA-N
Species of MetaboliteComponentSourceComments
Ustilaginoidea virens (ncbitaxon:1159556) - PubMed (36287930)
ChEBI Ontology
Outgoing Relation(s)
hemiustilaginoidin D (CHEBI:194134) is a benzochromenone (CHEBI:64986)
hemiustilaginoidin D (CHEBI:194134) is a naphtho-γ-pyrone (CHEBI:64542)
hemiustilaginoidin D (CHEBI:194134) is a phenols (CHEBI:33853)
IUPAC Name 
(2R,3R)-5,6,8-trihydroxy-2,3-dimethyl-2,3-dihydro-4H-naphtho[2,3-b]pyran-4-one
Synonyms  Source
(2R,3R)-2,3-dihydro-5,6,8-trihydroxy-2,3-dimethyl-4H-naphtho[2,3-b]pyran-4-oneChEBI
(2R,3R)-5,6,8-trihydroxy-2,3-dimethyl-2,3-dihydro-4H-benzo[g]chromen-4-oneIUPAC
Citations